NPASS Compound

Structure

CID302378 OpenBabel06191716112D 25 26 0 0 1 0 0 0 0 0999 V2000 -5.1962 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 4 2 0 0 0 0 3 7 1 0 0 0 0 4 10 1 0 0 0 0 5 6 2 0 0 0 0 5 10 1 0 0 0 0 6 11 1 0 0 0 0 7 22 1 0 0 0 0 8 10 2 0 0 0 0 8 12 1 0 0 0 0 9 18 1 0 0 0 0 11 12 2 0 0 0 0 11 24 1 0 0 0 0 12 23 1 0 0 0 0 13 9 1 1 0 0 0 13 14 1 0 0 0 0 13 25 1 0 0 0 0 14 15 1 0 0 0 0 14 19 1 6 0 0 0 15 16 1 0 0 0 0 15 20 1 1 0 0 0 16 17 1 0 0 0 0 16 21 1 6 0 0 0 17 24 1 1 0 0 0 17 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.15
Volume:	345.251
LogP:	-0.19
LogD:	0.19
LogS:	-1.472
# Rotatable Bonds:	7
TPSA:	117.84
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.518
Synthetic Accessibility Score:	3.655
Fsp3:	0.529
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.365
MDCK Permeability:	3.1081177439773455e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.753
Human Intestinal Absorption (HIA):	0.617
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.696

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.421
Plasma Protein Binding (PPB):	41.20252227783203%
Volume Distribution (VD):	0.325
Pgp-substrate:	19.50890350341797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.818
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.772
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.302
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.296
CYP3A4-inhibitor:	0.014
CYP3A4-substrate:	0.092

ADMET: Excretion

Clearance (CL):	2.162
Half-life (T1/2):	0.775

ADMET: Toxicity

hERG Blockers:	0.157
Human Hepatotoxicity (H-HT):	0.101
Drug-inuced Liver Injury (DILI):	0.119
AMES Toxicity:	0.502
Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.517
Carcinogencity:	0.676
Eye Corrosion:	0.004
Eye Irritation:	0.055
Respiratory Toxicity:	0.02

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC302378

Natural Product ID:	NPC302378
*Common Name:**	Methylconiferin
IUPAC Name:	(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[2-methoxy-4-[(E)-3-methoxyprop-1-enyl]phenoxy]oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	SCOBOZBTFMWPOO-AAHFWSMJSA-N
Standard InCHI:	InChI=1S/C17H24O8/c1-22-7-3-4-10-5-6-11(12(8-10)23-2)24-17-16(21)15(20)14(19)13(9-18)25-17/h3-6,8,13-21H,7,9H2,1-2H3/b4-3+/t13-,14-,15+,16-,17-/m1/s1
SMILES:	COC/C=C/c1ccc(c(c1)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3236506
PubChem CID:	5319561
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15019787]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22029392]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23517479]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	Latex Exudate	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3199	Balanophora involucrata	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3199	Balanophora involucrata	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2
Others	3

Activity Type	# Activity
Cell Line	4
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	19100.0	nM	PMID[469257]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	16500.0	nM	PMID[469257]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	32.9	%	PMID[469257]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	21.5	%	PMID[469257]
NPT862	Individual Protein	Epoxide hydratase	Homo sapiens	Inhibition	<	40.0	%	PMID[469257]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC302378 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	338
0.1-0.2	1545
0.2-0.3	4534
0.3-0.4	11117
0.4-0.5	7253
0.5-0.6	6124
0.6-0.7	7856
0.7-0.8	3141
0.8-0.85	530
0.85-0.9	192
0.9-0.95	55
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9918	High Similarity	NPC248355
0.9837	High Similarity	NPC472024
0.9837	High Similarity	NPC80600
0.9756	High Similarity	NPC26653
0.9756	High Similarity	NPC166040
0.9756	High Similarity	NPC270849
0.968	High Similarity	NPC162093
0.9603	High Similarity	NPC25821
0.9603	High Similarity	NPC49074
0.96	High Similarity	NPC9912
0.9597	High Similarity	NPC307110
0.9528	High Similarity	NPC187194
0.9453	High Similarity	NPC55040
0.9453	High Similarity	NPC470236
0.9449	High Similarity	NPC215833
0.9449	High Similarity	NPC69513
0.9444	High Similarity	NPC248307
0.9444	High Similarity	NPC65942
0.938	High Similarity	NPC164857
0.938	High Similarity	NPC37468
0.9375	High Similarity	NPC48863
0.9375	High Similarity	NPC476411
0.9375	High Similarity	NPC13745
0.9375	High Similarity	NPC251981
0.937	High Similarity	NPC299144
0.937	High Similarity	NPC252833
0.9308	High Similarity	NPC470413
0.9308	High Similarity	NPC138738
0.9297	High Similarity	NPC132895
0.9297	High Similarity	NPC6836
0.9237	High Similarity	NPC100389
0.9237	High Similarity	NPC212770
0.9237	High Similarity	NPC98777
0.9225	High Similarity	NPC470881
0.9225	High Similarity	NPC35731
0.918	High Similarity	NPC198734
0.918	High Similarity	NPC469412
0.9167	High Similarity	NPC210478
0.916	High Similarity	NPC59324
0.916	High Similarity	NPC65530
0.9141	High Similarity	NPC166168
0.9098	High Similarity	NPC60589
0.9098	High Similarity	NPC469708
0.9098	High Similarity	NPC76871
0.9084	High Similarity	NPC199459
0.9084	High Similarity	NPC52277
0.9084	High Similarity	NPC186418
0.9084	High Similarity	NPC203230
0.9084	High Similarity	NPC104167
0.9084	High Similarity	NPC177035
0.9084	High Similarity	NPC157554
0.9084	High Similarity	NPC242028
0.9077	High Similarity	NPC87696
0.9077	High Similarity	NPC107478
0.907	High Similarity	NPC470270
0.904	High Similarity	NPC287429
0.903	High Similarity	NPC469559
0.903	High Similarity	NPC60249
0.903	High Similarity	NPC475084
0.903	High Similarity	NPC157816
0.903	High Similarity	NPC189115
0.903	High Similarity	NPC246947
0.9024	High Similarity	NPC269242
0.9023	High Similarity	NPC202700
0.9023	High Similarity	NPC106944
0.9015	High Similarity	NPC304152
0.9015	High Similarity	NPC195196
0.9	High Similarity	NPC294166
0.9	High Similarity	NPC115022
0.8992	High Similarity	NPC473412
0.8992	High Similarity	NPC469698
0.8963	High Similarity	NPC46092
0.8963	High Similarity	NPC185307
0.8963	High Similarity	NPC478239
0.8963	High Similarity	NPC470950
0.8955	High Similarity	NPC469661
0.8947	High Similarity	NPC226005
0.8939	High Similarity	NPC25695
0.8939	High Similarity	NPC172818
0.8923	High Similarity	NPC26080
0.8923	High Similarity	NPC165686
0.8923	High Similarity	NPC303422
0.8923	High Similarity	NPC85799
0.8897	High Similarity	NPC471667
0.8897	High Similarity	NPC471063
0.8897	High Similarity	NPC79429
0.8897	High Similarity	NPC283995
0.8897	High Similarity	NPC217635
0.8897	High Similarity	NPC25292
0.8897	High Similarity	NPC129417
0.8897	High Similarity	NPC473045
0.8897	High Similarity	NPC470235
0.8889	High Similarity	NPC94276
0.8889	High Similarity	NPC109822
0.8889	High Similarity	NPC476356
0.888	High Similarity	NPC71090
0.888	High Similarity	NPC476142
0.8864	High Similarity	NPC238243
0.8846	High Similarity	NPC121376
0.8837	High Similarity	NPC86030
0.8837	High Similarity	NPC5851
0.8837	High Similarity	NPC97326
0.8837	High Similarity	NPC295970
0.8832	High Similarity	NPC475096
0.8832	High Similarity	NPC22150
0.8832	High Similarity	NPC279298
0.8832	High Similarity	NPC43508
0.8832	High Similarity	NPC38041
0.8832	High Similarity	NPC476301
0.8832	High Similarity	NPC18979
0.8828	High Similarity	NPC163332
0.8828	High Similarity	NPC118787
0.8828	High Similarity	NPC41706
0.8828	High Similarity	NPC292056
0.8828	High Similarity	NPC111247
0.8828	High Similarity	NPC147821
0.8828	High Similarity	NPC319625
0.8828	High Similarity	NPC183181
0.8824	High Similarity	NPC473044
0.8824	High Similarity	NPC252169
0.8819	High Similarity	NPC12308
0.8815	High Similarity	NPC472711
0.8815	High Similarity	NPC186406
0.8806	High Similarity	NPC156376
0.8797	High Similarity	NPC138350
0.8797	High Similarity	NPC40664
0.8797	High Similarity	NPC165482
0.8797	High Similarity	NPC197723
0.8797	High Similarity	NPC3293
0.8788	High Similarity	NPC130496
0.8788	High Similarity	NPC188555
0.878	High Similarity	NPC228907
0.8768	High Similarity	NPC112861
0.8768	High Similarity	NPC99515
0.8768	High Similarity	NPC476865
0.8768	High Similarity	NPC205796
0.8768	High Similarity	NPC199928
0.8768	High Similarity	NPC190714
0.8768	High Similarity	NPC276753
0.8768	High Similarity	NPC125755
0.876	High Similarity	NPC40377
0.876	High Similarity	NPC72529
0.8759	High Similarity	NPC232228
0.875	High Similarity	NPC58607
0.875	High Similarity	NPC191037
0.875	High Similarity	NPC140502
0.875	High Similarity	NPC178284
0.875	High Similarity	NPC48309
0.874	High Similarity	NPC114901
0.874	High Similarity	NPC293701
0.874	High Similarity	NPC48990
0.8731	High Similarity	NPC477798
0.8731	High Similarity	NPC477797
0.8731	High Similarity	NPC124149
0.8722	High Similarity	NPC184938
0.8722	High Similarity	NPC101624
0.871	High Similarity	NPC135961
0.8705	High Similarity	NPC224674
0.8705	High Similarity	NPC31325
0.8705	High Similarity	NPC227902
0.8705	High Similarity	NPC114505
0.8705	High Similarity	NPC275284
0.8705	High Similarity	NPC213074
0.8705	High Similarity	NPC15956
0.8705	High Similarity	NPC193473
0.8705	High Similarity	NPC39657
0.8702	High Similarity	NPC469613
0.8702	High Similarity	NPC30043
0.8702	High Similarity	NPC469625
0.8696	High Similarity	NPC476868
0.8696	High Similarity	NPC161700
0.8696	High Similarity	NPC469586
0.8696	High Similarity	NPC476869
0.8696	High Similarity	NPC476864
0.8696	High Similarity	NPC277867
0.8696	High Similarity	NPC476866
0.8692	High Similarity	NPC3439
0.8692	High Similarity	NPC210623
0.8692	High Similarity	NPC202582
0.8692	High Similarity	NPC226788
0.8692	High Similarity	NPC285339
0.8692	High Similarity	NPC222004
0.8692	High Similarity	NPC218003
0.8692	High Similarity	NPC190629
0.8692	High Similarity	NPC218856
0.8692	High Similarity	NPC470258
0.8692	High Similarity	NPC273295
0.8686	High Similarity	NPC113680
0.8686	High Similarity	NPC278961
0.8686	High Similarity	NPC477898
0.8682	High Similarity	NPC474119
0.8682	High Similarity	NPC198798
0.8676	High Similarity	NPC471908
0.8672	High Similarity	NPC194519
0.8672	High Similarity	NPC470510
0.8651	High Similarity	NPC226712
0.8651	High Similarity	NPC470804
0.8651	High Similarity	NPC266045
0.8647	High Similarity	NPC170694
0.8643	High Similarity	NPC175976

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC302378 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	283
0.1-0.2	855
0.2-0.3	1954
0.3-0.4	2834
0.4-0.5	1641
0.5-0.6	937
0.6-0.7	556
0.7-0.8	85
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8651	High Similarity	NPD1091	Approved
0.8413	Intermediate Similarity	NPD1357	Approved
0.8359	Intermediate Similarity	NPD3705	Approved
0.8322	Intermediate Similarity	NPD1653	Approved
0.8273	Intermediate Similarity	NPD6674	Discontinued
0.8271	Intermediate Similarity	NPD3027	Phase 3
0.8129	Intermediate Similarity	NPD7266	Discontinued
0.8088	Intermediate Similarity	NPD1613	Approved
0.8088	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7843	Approved
0.7823	Intermediate Similarity	NPD2684	Approved
0.782	Intermediate Similarity	NPD2983	Phase 2
0.782	Intermediate Similarity	NPD2982	Phase 2
0.7812	Intermediate Similarity	NPD7157	Approved
0.7794	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD228	Approved
0.7769	Intermediate Similarity	NPD291	Approved
0.7744	Intermediate Similarity	NPD2981	Phase 2
0.7742	Intermediate Similarity	NPD290	Approved
0.7724	Intermediate Similarity	NPD5058	Phase 3
0.7721	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD7054	Approved
0.7656	Intermediate Similarity	NPD5283	Phase 1
0.7622	Intermediate Similarity	NPD1375	Discontinued
0.7619	Intermediate Similarity	NPD556	Approved
0.761	Intermediate Similarity	NPD7472	Approved
0.761	Intermediate Similarity	NPD7074	Phase 3
0.7591	Intermediate Similarity	NPD3018	Phase 2
0.7556	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD4536	Approved
0.7535	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD4538	Approved
0.7517	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD37	Approved
0.7484	Intermediate Similarity	NPD3818	Discontinued
0.7469	Intermediate Similarity	NPD7808	Phase 3
0.7468	Intermediate Similarity	NPD4967	Phase 2
0.7468	Intermediate Similarity	NPD4965	Approved
0.7468	Intermediate Similarity	NPD4966	Approved
0.7464	Intermediate Similarity	NPD2861	Phase 2
0.7453	Intermediate Similarity	NPD6797	Phase 2
0.7451	Intermediate Similarity	NPD8455	Phase 2
0.7432	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD5536	Phase 2
0.7407	Intermediate Similarity	NPD7251	Discontinued
0.7397	Intermediate Similarity	NPD4236	Phase 3
0.7397	Intermediate Similarity	NPD4237	Approved
0.7376	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD7228	Approved
0.7372	Intermediate Similarity	NPD8651	Approved
0.7372	Intermediate Similarity	NPD6234	Discontinued
0.7362	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD5960	Phase 3
0.7361	Intermediate Similarity	NPD5588	Approved
0.7351	Intermediate Similarity	NPD3686	Approved
0.7351	Intermediate Similarity	NPD3687	Approved
0.7338	Intermediate Similarity	NPD2977	Approved
0.7338	Intermediate Similarity	NPD2978	Approved
0.7324	Intermediate Similarity	NPD1558	Phase 1
0.7315	Intermediate Similarity	NPD1774	Approved
0.7308	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7685	Pre-registration
0.7299	Intermediate Similarity	NPD3685	Discontinued
0.7297	Intermediate Similarity	NPD2677	Approved
0.7296	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7097	Phase 1
0.7286	Intermediate Similarity	NPD4908	Phase 1
0.7279	Intermediate Similarity	NPD1652	Phase 2
0.7279	Intermediate Similarity	NPD4162	Approved
0.7273	Intermediate Similarity	NPD1934	Approved
0.7273	Intermediate Similarity	NPD6671	Approved
0.7267	Intermediate Similarity	NPD4123	Phase 3
0.7254	Intermediate Similarity	NPD6233	Phase 2
0.7234	Intermediate Similarity	NPD3179	Approved
0.7234	Intermediate Similarity	NPD3180	Approved
0.723	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD4110	Phase 3
0.7226	Intermediate Similarity	NPD5772	Approved
0.7226	Intermediate Similarity	NPD5773	Approved
0.7222	Intermediate Similarity	NPD6653	Approved
0.7203	Intermediate Similarity	NPD3620	Phase 2
0.7203	Intermediate Similarity	NPD4060	Phase 1
0.7203	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7240	Approved
0.7188	Intermediate Similarity	NPD1358	Approved
0.7183	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD3817	Phase 2
0.7163	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD3060	Approved
0.7153	Intermediate Similarity	NPD1610	Phase 2
0.7153	Intermediate Similarity	NPD5735	Approved
0.7143	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4678	Approved
0.7143	Intermediate Similarity	NPD5762	Approved
0.7143	Intermediate Similarity	NPD6166	Phase 2
0.7143	Intermediate Similarity	NPD6842	Approved
0.7143	Intermediate Similarity	NPD6841	Approved
0.7143	Intermediate Similarity	NPD4675	Approved
0.7143	Intermediate Similarity	NPD5763	Approved
0.7143	Intermediate Similarity	NPD6843	Phase 3
0.7134	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD5846	Approved
0.7132	Intermediate Similarity	NPD6516	Phase 2
0.7132	Intermediate Similarity	NPD5125	Phase 3
0.7132	Intermediate Similarity	NPD1778	Approved
0.7132	Intermediate Similarity	NPD5126	Approved
0.7123	Intermediate Similarity	NPD4108	Discontinued
0.7115	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD4628	Phase 3
0.7113	Intermediate Similarity	NPD7095	Approved
0.7111	Intermediate Similarity	NPD1548	Phase 1
0.7109	Intermediate Similarity	NPD968	Approved
0.7105	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7526	Approved
0.7105	Intermediate Similarity	NPD52	Approved
0.7101	Intermediate Similarity	NPD2235	Phase 2
0.7101	Intermediate Similarity	NPD2231	Phase 2
0.7095	Intermediate Similarity	NPD2424	Discontinued
0.7091	Intermediate Similarity	NPD6559	Discontinued
0.708	Intermediate Similarity	NPD3496	Discontinued
0.7075	Intermediate Similarity	NPD2161	Phase 2
0.707	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6190	Approved
0.7063	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6798	Discontinued
0.7059	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2122	Discontinued
0.705	Intermediate Similarity	NPD4749	Approved
0.7045	Intermediate Similarity	NPD821	Approved
0.7034	Intermediate Similarity	NPD6355	Discontinued
0.7029	Intermediate Similarity	NPD776	Approved
0.7027	Intermediate Similarity	NPD3540	Phase 1
0.7025	Intermediate Similarity	NPD9365	Approved
0.7019	Intermediate Similarity	NPD3787	Discontinued
0.7014	Intermediate Similarity	NPD4062	Phase 3
0.7012	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2801	Approved
0.7	Intermediate Similarity	NPD4535	Phase 3
0.7	Intermediate Similarity	NPD6331	Phase 2
0.6993	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD2492	Phase 1
0.6977	Remote Similarity	NPD3134	Approved
0.6972	Remote Similarity	NPD9494	Approved
0.6968	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4140	Approved
0.6962	Remote Similarity	NPD2563	Approved
0.6962	Remote Similarity	NPD2560	Approved
0.6959	Remote Similarity	NPD3539	Phase 1
0.6957	Remote Similarity	NPD8127	Discontinued
0.6954	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD3022	Approved
0.6947	Remote Similarity	NPD3021	Approved
0.6944	Remote Similarity	NPD3145	Approved
0.6944	Remote Similarity	NPD3144	Approved
0.6934	Remote Similarity	NPD5585	Approved
0.6933	Remote Similarity	NPD5177	Phase 3
0.6928	Remote Similarity	NPD4739	Approved
0.6918	Remote Similarity	NPD447	Suspended
0.6918	Remote Similarity	NPD5124	Phase 1
0.6918	Remote Similarity	NPD1933	Approved
0.6918	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3882	Suspended
0.6918	Remote Similarity	NPD4340	Discontinued
0.6917	Remote Similarity	NPD5535	Approved
0.6909	Remote Similarity	NPD5844	Phase 1
0.6908	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD422	Phase 1
0.6901	Remote Similarity	NPD6584	Phase 3
0.6901	Remote Similarity	NPD558	Phase 2
0.6897	Remote Similarity	NPD2674	Phase 3
0.6892	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4625	Phase 3
0.6867	Remote Similarity	NPD7153	Discontinued
0.6863	Remote Similarity	NPD4357	Discontinued
0.6861	Remote Similarity	NPD1182	Approved
0.6857	Remote Similarity	NPD1608	Approved
0.6855	Remote Similarity	NPD9296	Approved
0.6849	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD2238	Phase 2
0.6846	Remote Similarity	NPD6032	Approved
0.6842	Remote Similarity	NPD2219	Phase 1
0.6835	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD1819	Approved
0.6831	Remote Similarity	NPD1820	Approved
0.6831	Remote Similarity	NPD1817	Approved
0.6831	Remote Similarity	NPD1818	Approved
0.6824	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3146	Approved
0.681	Remote Similarity	NPD3051	Approved
0.681	Remote Similarity	NPD6071	Discontinued
0.6809	Remote Similarity	NPD5327	Phase 3
0.6803	Remote Similarity	NPD230	Phase 1
0.68	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD5756	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data